In 1864, fourteen years before the construction of 'Glenroy' in 1878, the railway had sliced a line through Windsor. By the 1880s, the few existing cottages in the bush south of the railway line had been joined by newer dwellings becoming the embryonic suburb later known as Newtown. Widow Elizabeth Hoskisson sold her investment house (Glenroy) and four George Street allotments to Richard William Cobcroft and his wife Gertrude in 1888. A year or so before, Richard had taken over George Carroll&#39;s tannery located nearby on the corner of Mileham and Argyle Streets. Improving fortunes and the pressures of a fourth and fifth child gave impetus to expand 'Glenroy&#39; from six to twelve rooms by 1894. A desire for a grander lifestyle saw the Cobcrofts engage James Mullinger, the original builder to evolve the dwelling from a comfortable, traditional four-roomed brick cottage with a bell-eaved verandah supported by wooden posts, to a stylish, extravagant Victorian villa with an encircling iron-laced verandah and roof finials. Renovated servant's quarters and kitchen, horizontal slab stables, extensive rose gardens and a croquet lawn allowed gracious living and spacious grounds for charity bazaars. 'Glenroy'; acquired rare running hot water, a laundry and a state-of- the-art outside toilet. In 1890, Richard indulged in a billiard room featuring a front bay window and clerestory windows in a lantern roof space, to help light the full-sized table. He entertained wealthy local and Sydney men, many of them successful entrepreneurs within the leather industry who held regular social and official billiard competitions in their homes. The distinctive billiard room colour scheme of aqua and brown was repeated in a showpiece ballroom (reportedly built for a daughter's wedding) two years later. This final grand addition ensured 'Glenroy'; was a place of significance, and the highest rated house in the neighbourhood. Sporting the very latest in decorated pressed-metal ceilings, the entire room was a statement of fashion. Its ostentatious brown-red marble fireplace with black panels was tiled in tones to echo the ceiling highlights, and the skirting board was of extreme proportions. In 1894 the family purchased the remaining four Hoskisson allotments which fronted Church Street, allowing room for the cow shed, ceramic bottle paths and duck pond. A weatherboard bedroom addition and an office completed the Cobcroft house. The office built into a corner of the verandah is visually the most unimposing room of all, and yet it is arguably the most important. Within its walls Richard kept his accounts for the tannery. This room has its own entry stairs, quite distinct from the front entry, the main entry and the servant's steps. A total separation of home-work roles. Conversion to flats, land sale and neglect all took their toll, but conservation and restoration has once more revealed the charms of 'Glenroy'; preserved in a garden setting which cares for the two huge melaleuca trees that survive proudly as remnant original bush.